Ethyl Acetate → Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

HRID 40624

反応式

HRID 40624 の反応式
COC1C=C(OC)C=CC=1C[N:6]1[C:13](=[O:14])[C@H:12]2[N:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[C:16](=[O:17])[C@@H:7]1[CH2:8][CH:9]=[CH:10][CH2:11]2.C(OCC)(=O)C>FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1.CCCCCCC>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[N:15]1[C:16](=[O:17])[C@H:7]2[NH:6][C:13](=[O:14])[C@@H:12]1[CH2:11][CH:10]=[CH:9][CH2:8]2

参加物

6

反応物 2

HCID 8857Ethyl Acetate2 回HCID 69230528Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

生成物 1

HCID 69230546Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

試薬・触媒・溶媒 3

HCID 6422Trifluoroacetic acid溶媒HCID 7520Thioanisole溶媒HCID 8900Heptane溶媒

実験手順

Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione (0.180, 0.406 mmol) was placed in a CEM microwave 10-mL pressure-rated tube and was dissolved in trifluoroacetic acid (4.25 mL) and thioanisol (0.05 mL). The reaction mixture was capped and heated in a CEM discover system laboratory microwave at 120° C. for 0.5 hours. The reaction mixture was poured into a 100 mL round bottom flask and Celite® (approximately 5 g) and ethyl acetate (20 mL) were added. The solvents were removed. The Celite®/reaction mixture was loaded into an Isco solid phase loading cartridge. Flash chromatography was carried out using an Isco Companion automated chromatography system, silica column (12 g), initially holding at 40% ethyl acetate in heptane for 8 column volumes, increasing the ethylacetate concentration to 100% over 3 column volumes, holding at 100% ethyl acetate for 20 more column volumes to yield a residue.

後処理

  1. customThe reaction mixture was capped
  2. temperatureheated in a CEM
  3. customat 120° C.
  4. customfor 0.5 hours
  5. additionThe reaction mixture was poured into a 100 mL round bottom flask
  6. customThe solvents were removed
  7. customThe Celite®/reaction mixture
  8. temperatureincreasing
  9. concentrationthe ethylacetate concentration to 100% over 3 column volumes
  10. customto yield a residue

出典と根拠

ORDレコード
ord-1069adaef9074f0187f577692185ade6
出典データセット
uspto-grants-2013_09
特許番号
US08530475B2

関連ノート

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